Amination of α,β-Unsaturated (2-Trimethylsilanylmethyl) Carboxylic Esters.

Abstract The reactions of (2-trimethylsilanylmethyl) α,β-unsaturated carboxylic ethyl esters with NsONHCO 2 Et and CaO produce, after treatment with AcOH, α-methylene N -(ethoxycarbonyl) β-amino carboxylic esters through ring opening and elimination of the trimethylsilyl group from the intermediate aziridine. By ozonization and subsequent reductive cleavage these products give the corresponding N -(ethoxycarbonyl) β-amino α-hydroxy esters.